Here is the best analysis I think anyone can put together on how possible it is. None of this "If Matthews just scores 40 goals a year for 12 more years" crap.
Let's give Matthews a big benefit of the doubt and ASSUME that he will score 110 goals in the next 2 years (55 per year). That would require him to:
a) Stay healthy, which is never a given
b) Score at a rate much higher than 2 of his last 3 seasons, which is still possible as he has peaked way above that. But when looking at a player entering that age where statistically goalscoring starts to fall off, it is still a stretch goal for sure.
So, starting from age 30 season onwards:
What I have here is a chart of all of the 'x' aged goal scoring seasons.
For example, the highest goal total for a 30-year-old is 69, the 2nd is 55, the 20th is 42 goals.
-> Note: I removed Ovechkin from these totals, as Ovi is the biggest anomaly and holds a bunch of these statistical records for x-aged totals.
The result, Matthews would need to do BOTH of the following:
a) Play until 40 years old,
b) Finish on average, with the 5th best goal total for each age from 30 to 40.
That would put him around where Ovi will finish.
The question then becomes, how hard will it be for him to do those 2 things above?
a) Play until 40 years old:
Pretty unlikely that he even plays out his 39/ or 40 year old season. It just doesn't happen very often. Look at the last 10 years and how hard it is to stay in this league at 39 or 40 years old.
And those few guys in this sample who did play out a 40 year old season were putting up like 10 goals or less lol.
b) Averages with the 5th best goal total for his age group:
He has done this exactly 2 times out of his 9 year career.... unlikely to do it for 13 more years LOL.